Water → HCID 15138852, compound

HRID 1858894Notes

Reaction equation

HRID 1858894 reaction equation
C(Cl)(Cl)(Cl)Cl.O.[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[CH2:19][OH:20])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C[CH2:22][O:23]CC>>[CH2:7]([O:14][CH2:15][C@H:16]1[O:18][C@H:17]1[C:19]([O:23][CH3:22])=[O:20])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 962Water2×HCID 3283Diethyl EtherHCID 5943Carbon TetrachlorideHCID 9815529HCID 9815529, compound

Product 1

HCID 15138852HCID 15138852, compound

Conditions

Temperature
0 °C

Procedure

To a solution of 10 ml CCl4, 10 ml CH3CH, and 15 ml of H2O was added 50 mg of RuCl3 --H2O and 1.00 g (5.16 mmole) of (2S-cis)-3-(benzyloxymethyl)oxirane methanol. The solution was cooled to 0° C. and 3.50 g (15.5 mmole) of H5IO6 was added in portions over 15 min with vigorous stirring. The reaction was allowed to stir vigorously for 2 hours. The mixture was poured into 100 ml of Et2O, the organic layer separated and the aqueous layer washed with 20 ml of Et2O. The combined organic layers were washed four times with 50 ml 0.1 N NaOH. The aqueous layers were combined, acidified to pH 2, and extracted three times with 50 ml Et2O. The ether layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue.

Workup

  1. customthe organic layer separated
  2. washthe aqueous layer washed with 20 ml of Et2O
  3. washThe combined organic layers were washed four times with 50 ml 0.1 N NaOH
  4. extractionextracted three times with 50 ml Et2O
  5. dry with materialThe ether layers were dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield a pale yellow residue

Sources & evidence

ORD record
ord-7709b64b5c2449e4af4d7f885312e4f9
Source dataset
uspto-grants-2000_11
Patent number
US06153589

Reaction notes

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